The last time that Justin Osborne of up-and-coming alt-country band Susto tried to cross into Canada for a show in Vancouver, three border security agents threatened to put the brakes on his plans.

“When I was on a solo tour, I tried to sneak into the country to play a free concert at a coffee shop,” the American singer and guitarist tells the Straight on the line from a Detroit tour stop. “It was the Fourth of July, and my girlfriend and I had a weed pipe in the car. It didn’t have any marijuana in it, but we figured we should hide it. When we came up to the border, the guards pulled us over. I’d just got ACID BOYS tattooed on my knuckles, so I could see why they’d think we were suspicious.

“We were praying that we wouldn’t get fined, because we were completely broke, and we were way across the country from our families. They asked, ‘Is there anything in the car that you want to tell us about?’ So we explained about the bowl, and that it was all cleaned out. After they finished searching, they pulled us aside. They said, ‘We found the pipe—thank you for being honest with us. And you’re both under arrest.’

“My girlfriend and I turned to each other, and we were thinking, ‘Holy shit—what are we going to do?’ And then the officers looked around and started cracking up. They said, ‘Just kidding—welcome to Canada.’ We ended up having one really cool, interesting night in Vancouver. They got us for sure.”

With a ready chuckle, Osborne is an engaging storyteller. Re-counting tales from both good and bad moments in his life, he speaks in forensic detail of the experiences that took him from being a churchgoing Protestant in the American South to a rebellious touring musician living it up on the road. That honesty is, Osborne says, a new thing. Attributing its development to his time living in Cuba, the South Carolina native has let the trait transform both his attitude to life and his method of songwriting.

“I started playing in bands when I was 13,” the singer recalls. “I created my old group, Sequoyah Prep School, in my late teens, and I was in that band until I was 26. We toured a lot and put out three albums. Nine years later, I got tired of playing songs that I’d written early on. I just didn’t feel like I could relate to them anymore. So I put music down, and gave it all up.

“A few years after that, I started Susto as a casual project to work on,” he continues. “I felt like I was holding back in my old band lyrically, because I was worried about what my parents would think. With Susto, I learned to let loose, and that it’s okay to sing about dark stuff in a flirtatious way, and to tell the truth without holding back or censoring myself. When I started writing like that, the repercussions definitely came. For a while, my family didn’t even want to talk to me. My old fans from Sequoyah Prep School didn’t like it either, because it wasn’t as sunshiny or singsongy. But it was worth it for the songs to be able to come from an authentic place.”

Susto’s latest release, & I’m Fine Today, is testament to the power of that truth-telling. The 11-track sophomore album by the five-piece takes listeners on a deeper exploration of Osborne’s psyche. Framed by the singer’s southern drawl and soft acoustic-guitar chords, tracks like “Hard Drugs” balance a straight-talking story with tight harmonies—a theme that runs through the record as a whole.

More cinematic and nuanced than the band’s first LP, & I’m Fine Today introduces a new palette of sounds, including string sections, funk bass lines, and Caribbean rhythms that adeptly scaffold the songs’ emotional narratives.

“I think the track ‘Far Out Feeling’ best matches the music and lyrics,” Osborne says. “The summer I wrote it, my two brothers were going through rehab, my dad got cancer, and I’d just quit everything to tour across the country. I felt as if we were never going to break through, and I wanted it so badly—not just for me, but for my family. That song is definitely the most dramatic on the album, and I’m glad that we were able to take those feelings and translate them sonically.”

The emotional poignancy of & I’m Fine Today has propelled the group to new heights. Personally picked by Grammy nominees the Lumineers to open on their latest tour, Susto is currently finishing up a slew of support slots for the Americana giants before embarking on its own headline performances.

“It’s a real privilege to play to so many people every night,” Osborne says. “It’s often at least 5,000. We’ve seen that growth in the social-media world, and also we’ve seen it when we top the bill. People are coming out to see us, and it feels like individuals are starting to pay attention. We’re selling out shows by ourselves in cities that I never would have dreamed of. I always prayed that we’d be able to do this. If the band never got any bigger than what it is now, I’d still be happy.”

Susto plays the Cobalt on Monday (April 3).